Regiodivergent cyclobutanone cleavage: switching selectivity with different Lewis acids

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Strain release in small rings is a key driver for synthetic transformations.
• Cyclobutanones are versatile substrates for creating diverse molecular building blocks.

Purpose of the Study:

• To present Lewis acid-catalyzed rearrangement reactions of cyclobutanones.
• To achieve selective synthesis of two distinct polycyclic scaffolds.

Main Methods:

• Utilizing Lewis acid catalysis for cyclobutanone rearrangement.
• Investigating the influence of Lewis acids on reaction pathways and regioselectivity.

Main Results:

• Selective access to indenylacetic acid derivatives was achieved.
• Selective access to benzoxabicyclo[3.2.1]octan-3-ones was achieved.
• Lewis acid choice dictates reaction outcome and C-C bond cleavage site.

Conclusions:

• Lewis acid catalysis offers a powerful method for cyclobutanone transformations.
• The judicious selection of Lewis acids enables controlled synthesis of complex polycyclic structures.